Deck 20: The Chemistry of Carboxylic Acids

Question 1

Name the carboxylic acid.

Answer 1

The longest chain containing the carboxylic acid is highlighted in red below. The name is 2,5-dimethylheptanoic acid.

Question 2

Name the carboxylic acid using Greek letters, rather than numbers.

Answer 2

As in aldehydes and ketones, the carbons next to the functional group can be denoted by Greek letters. There are four carbons in the molecule, so the parent chain is butyric acid. The hydroxy group is on the beta carbon, so the name is $\beta$ -hydroxybutyric acid.

Question 3

Give the IUPAC and common name for the dicarboxylic acid.

Answer 3

The dicarboxylic acid has the IUPAC name propanedioic acid and the common name, malonic acid.

Question 4

Rank the functional groups in order of highest priority to lowest for nomenclature.

A) alcohol > aldehyde > carboxylic acid > thiol
B) aldehyde > carboxylic acid > thiol > alcohol
C) thiol > carboxylic acid > aldehyde > alcohol
D) carboxylic acid > aldehyde > alcohol > thiol

Question 5

Draw the structure of the nucleophile (including formal charges) that would give the product on the right.

Question 6

Draw the structure of the nucleophile (including formal charges) that would give the product on the right.

Question 7

Predict the major organic product for the reaction. If you believe no reaction will occur, write NR.

Question 8

Outline a synthesis to prepare the ester from cyclohexene.

Question 9

Provide structures for products A-D. The ¹H NMR spectrum of D is given.
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Question 10

Predict the major organic product for the reaction. If you believe no reaction would occur, write NR.

Question 11

Which compound decarboxylates fastest?

A) compound A
B) compound B
C) compound C
D) compound D
E) compound E

Question 12

Provide a detailed, arrow-pushing mechanism for this transformation. Show all reactive intermediates and all proton transfer steps. At some point in your answer, show the two most important resonance structures for diazomethane, CH₂N₂, and identify the gas that is produced in the reaction.

Question 13

Which side is favored at equilibrium?

A) the left
B) the right
C) need to know pK_a values of the individual acids before estimating
D) the equilibrium depends on the temperature of the measurement, and thus can't be known
E) neither, K_eq = 1

Question 14

Which of the carboxylic acids would not decarboxylate (lose CO₂) upon warming?

A) compound A
B) compound B
C) compound C
D) compound D
E) neither compound C nor compound D would decarboxylate upon warming

Question 15

A student has synthesized two isomers, A and B, but neglected to label the flasks. Suggest a spectroscopy method the student could use to quickly differentiate between them and explain what feature they would be looking for.

Question 16

A compound with the formula C₉H₁₀O₂ has this ¹H NMR spectra. Deduce the structure.

Question 17

Which statement is true of soaps?

A) Soap is made by reduction of a fatty acid.
B) Soap is positively charged.
C) Soap has a long hydrocarbon tail and ionic head group.
D) Soap molecules form micelles, where the polar head groups are on the inside of the ball and the tails are on the outside.

Question 18

Outline a multistep synthesis to perform the transformation.

Question 19

Outline a multistep synthesis of the ketone from the carboxylic acid.

Question 20

Predict the major organic product for the reaction.

Question 21

Outline a one-step synthesis of the anhydride.

Question 22

Predict the major organic product for the reaction.

Question 23

Outline a multistep synthesis of the transformation.

Question 24

Outline a multistep synthesis of the transformation.

Question 25

Draw a curved arrow mechanism for the esterification.